Model
Digital Document
Publisher
Florida Atlantic University
Description
The stereoselectivity ofthe Diels-Alder reaction of cyclopentadiene and maleic
anhydride towards its exo adduct was improved in perfluorinated solvents, in comparison
to a reaction carried out in hydrocarbon solvents and a solvent free reaction. When using
FC-70, the reaction of in situ generated cyclopentadiene and maleic anhydride produced
exo- norbomene-cis-5,6-dicarboxylic anhydride and endo- norbomene-cis-5,6-
dicarboxylic anhydride in a ratio of 52:32 according to GC-MS analysis. In hydrocarbon
solvent, mesitylene, the ratio of exo/endo was found to be 23:52, indicating a more
kinetically-controlled reaction. Separation of the reaction products by radial
chromatography provided the endo adduct in 89% purity and the exo adduct in 47%
purity.
anhydride towards its exo adduct was improved in perfluorinated solvents, in comparison
to a reaction carried out in hydrocarbon solvents and a solvent free reaction. When using
FC-70, the reaction of in situ generated cyclopentadiene and maleic anhydride produced
exo- norbomene-cis-5,6-dicarboxylic anhydride and endo- norbomene-cis-5,6-
dicarboxylic anhydride in a ratio of 52:32 according to GC-MS analysis. In hydrocarbon
solvent, mesitylene, the ratio of exo/endo was found to be 23:52, indicating a more
kinetically-controlled reaction. Separation of the reaction products by radial
chromatography provided the endo adduct in 89% purity and the exo adduct in 47%
purity.
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